Trifluoroacetic acid → HCID 57640339, compound
Reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][CH:18]([N:21]([CH2:27][C:28]2[O:29][C:30]3[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=3[CH:32]=2)[CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:17][CH2:16]1)=O)(C)(C)C>ClCCl>[CH3:25][CH:24]([CH3:26])[CH2:23][CH2:22][N:21]([CH2:27][C:28]1[O:29][C:30]2[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=2[CH:32]=1)[CH:18]1[CH2:17][CH2:16][NH:15][CH2:20][CH2:19]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Trifluoroacetic acid (15 ml, 195 mmol) is added to a solution of 4-{[(benzofuran-2-yl)methyl]-(3-methylbutyl)-amino}-piperidine-1-carboxylic acid tert-butyl ester (1.17 g, 2.92 mmol) in dichloromethane (15 ml). The reaction is stirred overnight at room temperature. The reaction is concentrated and water added to the residue. The solution is loaded onto a SCX-2 (10 g) column and washed with water (20 ml) and methanol (20 ml). The product is then eluted off with 2M ammonia in methanol (30 ml) and concentrated on a rotary evaporator to yield (0.77 g) of N-(3-methylbutyl)-N-[(benzofuran-2-yl)methyl]piperidin-4-amine: mass spectrum (ion spray): m/z=301 (M+1); 1H NMR (CDCl3): δ=7.52-7.43 (2H, m), 7.25-7.16 (2H, m), 6.56 (1H, s), 3.81 (2H, s), 3.14 (2H, brd), 2.72-2.52 (5H, m), 1.86-1.75 (3H, brm), 1.64-1.34 (5H, m), 0.92-0.83 (6H, m).